1. Field of the Invention
The present invention relates to a process for production of 2,6-dimethylnaphthalene and more particularly to a process for producing 2,6-dimethylnaphthalene on a commercial scale from toluene, n-butene and carbon monoxide as starting materials to produce p-tolyl sec-butyl ketone.
2. Description of the Related Arts
2,6-Dimethylnaphthalene is generally used as a starting material for producing industrially useful 2,6-naphthalene dicarboxylic acid through oxidation. This 2,6-naphthalene dicarboxylic acid is used, for example, for producing polyethylene terephthalate fibers or films having excellent tensile strength and thermal resistance.
2,6-Dimethylnaphthalene which is such a useful chemical material, has heretofore been obtained by isolating it from a tar fraction. However, in this method of isolating from a tar fraction, only a small amount of 2,6-dimethylnaphthalene can be obtained and moreover its separation or purification is difficult. Thus this method using a tar fraction as a starting material cannot be said to be a method suitable for industrial production of 2,6-dimethylnaphthalene in large quantities and at low production costs.
In recent years, various methods of synthesizing 2,6-dimethylnaphthalene from various starting materials have been proposed. In fact, however, no industrial methods of production whereby 2,6-dimethylnaphthalene can be synthesized effectively and selectively from an inexpensive starting material have been developed.
For example, Japanese Patent Publication Nos. 17983/1975, 17984/1975 and 17985/1975 disclose methods in which 5-(o-tolyl)pentene-2 is used as a starting material and it is subjected to dehydrogenation and cyclization to produce 2,6-dimethylnaphthalene and other dimethylnaphthalenes. In general, the 5-(o-tolyl)pentene-2 to be used as a starting material in the above method is synthesized from o-xylene and 1,3-butadiene. In this reaction, however, alkylation of the methyl group in the o-xylene is unpractical and, therefore, the production of 5-(o-tolyl)pentene-2 itself is not easy. Also during the dehydrogenation and cyclization steps of 5-(o-tolyl)pentene-2, a number of dimethylnaphthalene isomers other than 2,6-dimethylnaphthalene are formed and, therefore, an isomerization step and a complicated separation and purification step are required.
Japanese Patent Publication Nos. 1701/1976 and 5292/1978 disclose methods in which an alkylated product from toluene or p-xylene is used as a starting material and it is subjected to dehydrogenation and cyclization to produce various types of dimethylnaphthalenes, as well as 2,6-dimethylnaphthalene. In particular, Japanese Patent Publication No. 5292/1978 discloses a method in which 3-methyl-4-(p-tolyl)-butane obtained by the side chain alkylation of p-xylene with butene-1 is used as a starting material and it is subjected to dehydrogenation and cyclization to produce 2,6-dimethylnaphthalene. However, since a large amount of an alkali metal such as sodium or potassium is generally used in the side chain alkylation, the starting material itself becomes expensive. Moreover, in the dehydrogenation and cyclization reaction of the starting material, a number of dimethylnaphthalene isomers other than 2,6-dimethylnaphthalene are also produced. Thus the above method cannot be said to be an industrially satisfactory method.